Potassium Carbonate → HCID 178461463, compound

HRID 657615Notes

Reaction equation

HRID 657615 reaction equation
Cl.Cl[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][C@@H:10]([CH3:12])[CH2:9][C@H:8]([CH3:13])[CH2:7]1.[CH3:14][N:15]([CH3:29])[C@H:16]1[CH2:21][CH2:20][C@H:19]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)[CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:14][N:15]([CH3:29])[C@H:16]1[CH2:17][CH2:18][C@H:19]([C:22]2[CH:23]=[CH:24][C:25]([O:28][CH2:3][CH2:4][CH2:5][N:6]3[CH2:11][C@@H:10]([CH3:12])[CH2:9][C@H:8]([CH3:13])[CH2:7]3)=[CH:26][CH:27]=2)[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 131729321HCID 131729321, compoundHCID 178483999HCID 178483999, compound

Product 1

HCID 178461463HCID 178461463, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A A mixture of (3S,5S)-1-(3-chloropropyl)-3,5-dimethylpiperidine, hydrochloride (2.04 g), trans-N,N-dimethyl-4-(4-hydroxyphenyl)cyclohexanamine (1.98 g) and potassium carbonate (5.0 g) in N,N-dimethylformamide is stirred at a temperature close to 60° C. overnight. The precipitate is filtrated. The filtrate is concentrated under reduced pressure, purified by chromatography over silica gel with a gradient dichloromethane/methanol/ammonia from 90/10/1 to 80/20/1. Fractions containing the expected product are pooled, concentrated under reduced pressure to give 2.25 g of (3S,5S)-1-{3-[4-(trans-4-dimethylaminocyclohex-1-yl)phenoxy]propyl}-3,5-dimethylpiperidine. The base is dissolved in ethanol and converted to the hydrochloride by addition of ethanolic hydrogen chloride. Recrystallisation in ethanol affords 1.93 g of (3S,5S)-1-{3-[4-(trans-4-dimethylaminocyclohex-1-yl)phenoxy]propyl}-3,5-dimethylpiperidine, dihydrochloride as a white powder melting at 240° C.

Workup

  1. customclose to 60° C. overnight
  2. filtrationThe precipitate is filtrated
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. custompurified by chromatography over silica gel with a gradient dichloromethane/methanol/ammonia from 90/10/1 to 80/20/1
  5. additionFractions containing the expected product
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-77e15c5e49c44fbf9577bd3226ab2ab7
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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